Methanol → HCID 86721005, compound

HRID 524949Notes

Reaction equation

HRID 524949 reaction equation
N[C:2]1[C:13]([C:14]([O:16]N2C3C=CC=CC=3N=N2)=O)=C2N=CC(CC#N)=CN2N=1.[N+:26]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][C:34]=1[C:35]1[CH2:36][CH2:37][NH:38][CH2:39][CH:40]=1)([O-:28])=[O:27].O1CC(=O)C1.CO>C1COCC1>[N+:26]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][C:34]=1[C:35]1[CH2:36][CH2:37][N:38]([CH:13]2[CH2:14][O:16][CH2:2]2)[CH2:39][CH:40]=1)([O-:28])=[O:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 150242543-OxetanoneHCID 86721004HCID 86721004, compoundHCID 901998921H-benzo[d][1,2,3]triazol-1-yl 2-amino-6-(cyanomethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

Product 1

HCID 86721005HCID 86721005, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium triacetoxyborohydride (Sodium Ion (1)) (1.189 g, 5.608 mmol) was added in portions to a stirred solution of 3-nitro-4-(1,2,3,6-tetrahydropyridin-4-yl)pyridine (523 mg, 2.549 mmol) and 3-oxetanone (312.2 mg, 277.8 μL, 4.333 mmol) in THF (10 mL) at 0° C. under an atmosphere of nitrogen. The reaction was allowed to warm to ambient temperature and was stirred for 16 hours. MeOH (2 mL) was added dropwise and the mixture stirred at ambient temperature for 30 minutes. The mixture was concentrated in vacuo and the residue was partitioned between water and EtAOc. The pH of the aqueous layer was adjusted to pH 7-8 by the addition of NH4OH and the layers separated. The aqueous layer was extracted with EtOAc (×3) and the combined organic extracts washed with brine (×1), dried (MgSO4), filtered and concentrated in vacuo to give 3′-nitro-1-(oxetan-3-yl)-1,2,3,6-tetrahydro-4,4′-bipyridine as a red oil (615 mg, 92% Yield). MS (ES+) 262.1.

Workup

  1. stirringthe mixture stirred at ambient temperature for 30 minutes
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was partitioned between water and EtAOc
  4. additionThe pH of the aqueous layer was adjusted to pH 7-8 by the addition of NH4OH
  5. customthe layers separated
  6. extractionThe aqueous layer was extracted with EtOAc (×3)
  7. washthe combined organic extracts washed with brine (×1)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a6a7fd7b4f74ccca34ba7a12020d13e
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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